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Isle of Wight Short Breaks

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Your Isle of Wight search returned 168 cottages

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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Woodlands is a charming, pet-friendly house situated near Freshwater in the Isle of Wight, with a woodburning stove, conservatory, and countryside views. Yarmouth 3.3 miles; Cowes 15.8 miles; Fishbourne 17.1 miles; Ryde 18.9 miles. (Ref. 1176308)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $1052

  • Sleeps4
  • Bedrooms1
  • Pet FriendlyNo

    4.7

    Outstanding

  • Sykes rating

No. 5 Cliffview is a spectacular ground-floor apartment overlooking the coast in Ventnor, on the Isle of Wight. Open-plan. Ground-floor living. Close to the beach. Romantic. Newport 11.9 miles; Cowes 16 miles. (Ref. 1069835)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Thu 5th Mar 2026 to 1st Jan 2027


for 3 nights From $593

Last booked 2 days ago
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  • Sleeps12
  • Bedrooms4
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Tall Timbers, a lovely coastal cottage set in the Victorian town of Ventnor in Isle of Wight, enjoying a pet-friendly policy and a short walk to a beach. Newport 11.5 miles; Cowes 16 miles. (Ref. 1163988)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $945

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Hayloft is a first-floor, pet-friendly apartment situated in Bonchurch near the seaside town of Ventnor, Isle of Wight, and is set just a short walk from the beach. Newport 12.1 miles; Cowes 16.5 miles. (Ref. 1167864)

  • Pets go free
  • Off-road parking
  • Washing machine
  • Baby-friendly


for 3 nights From $511

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

A lovely, three-bedroom eco lodge sitting in Pondwell near Seaview, Isle of Wight. Open-plan. Near a beach. Hot tub. Country views. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1083787)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine


for 3 nights From $862

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A delightful, single-storey stable conversion resting in Brighstone, Isle of Wight. Family and pet-friendly. Close to amenities and the beach. Contemporary. In AONB. Open-plan. Enclosed garden. Newport 8.5 miles; Yarmouth 8.8 miles; Cowes 12.3 miles. (Ref. 1129624)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $609

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.4

    Good

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Comfortable and spacious ground floor studio apartment situated on the beach, 10 minutes from Yarmouth. Wonderful sea views. Perfect for a romantic retreat. (Ref. 4220)

  • Pet friendly (extra charges may apply)
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom


for 3 nights From $396

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.1

    Good

  • Sykes rating

A lovely country-style cottage resting in Shorwell, Isle of Wight. Beautiful views. Close to amenities. Pet-friendly. Close to walking trails. Newport 5.6 miles; Yarmouth 9.4 miles. (Ref. 1108496)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From $733

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    3.3

  • Sykes rating

The Shingles is a traditional property situated in the coastal town of Sandown, Isle of Wight. Beach nearby. TV. Garden. Shanklin 1.5 miles; Ryde 6.9 miles. (Ref. 1148748)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 3 nights From $494

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Glebe Garth is a charming, pet-friendly detached holiday home situated in the village of Chale near Niton on the Isle of Wight with a private hot tub. Ventnor 7 miles; Shanklin 8.8 miles. (Ref. 1172215)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $917

Last booked yesterday
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  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.2

    Good

  • Sykes rating

Morningside is a delightful, detached property resting in the seaside town of Totland Bay, Isle of Wight. Close to a shop and a pub. Near AONB. Near a beach. Freshwater 0.8 miles; Afton 1.7 miles; Newport 11.9 miles. (Ref. 1152560)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $1137

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    3.9

    Good

  • Sykes rating

A remarkable three-bedroom holiday home resting in Sandown, on the Isle of Wight. Open-plan. Family-friendly. Close to the beach. Ryde 6.5 miles; Cowes 14 miles; Yarmouth 18.9 miles. (Ref. 1073331)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $729

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

A contemporary, single-storey stable conversion located in Brighstone, Isle of Wight. Enclosed garden. Open-plan. In AONB. Close to amenities. Pet-friendly. Near the coast. Newport 8.5 miles; Yarmouth 8.8 miles; Cowes 12.3 miles. (Ref. 1005142)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $573

Last booked 8 hours ago
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  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Champagne is a fabulous three-bedroom eco lodge resting in Pondwell near Seaview, Isle of Wight. Open-plan. Country views. Near a beach. Off-road parking. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1083788)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine


for 3 nights From $862

Holiday Park

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

117 Crosswinds is a contemporary single-storey lodge with on-site facilities, located near a beach on the outskirts of Bembridge, on the Isle of Wight. Ryde 7.6 miles; Newport 10.7 miles; Cowes 15.2 miles; Yarmouth 20 miles. (Ref. 1165420)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $623

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.3

    Good

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Superb first floor, open plan, loft-style apartment right on the beach, west of Yarmouth on the Isle of Wight. Sensational sea views. Perfect for families. (Ref. 4221)

  • Wi-fi
  • Off-road parking


for 3 nights From $435

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.2

    Good

  • Sykes rating

Well-presented detached bungalow set in the heart of Upton, Isle of Wight. Open plan accommodation. Sandown and Newport 7 miles. (Ref. 942766)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $461

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Medina by The Solent is a pleasant, first-floor apartment situated by the sea in Cowes, Isle of Wight, well-positioned to nearby beaches, shops, and pubs. Newport 5.2 miles; Ryde 12.6 miles; Shanklin 14.5 miles; Ventnor 15.5 miles; Freshwater 15.7 miles. (Ref. 1166333)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights From $422

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.2

    Good

  • Sykes rating

A delightful, terraced cottage situated in the hamlet of Afton, near Freshwater, Isle of Wight. Pet-friendly. Off-road parking. Close to amenities and beach. Enclosed patio garden. Yarmouth 2.9 miles; Cowes 14.1 miles; Fishbourne 14.9 mile Please note: s. (Ref. 1108633)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $480

  • Sleeps3
  • Bedrooms1
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Delightful beachfront cottage apartment. Tranquil, rustic open plan living accommodation. Only seconds from beach. Panoramic picturesque coastal views across the Solent. Café/ bistro next door. Newport 12 miles. (Ref. 905105)

  • Pets go free
  • Wi-fi
  • Off-road parking


for 3 nights From $457

Last booked 2 days ago
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